250 PRACTICAL ORGANIC CHEMISTRY The second yields, in acetic acid solution, formasyl derivatives, CHUCO.CHo.COOCoH, -t- CrII,N,Cl = CM ..CO CH:N.NH.Q.II ' ' +"co2-!-c2r-isOH + CH3.CO.CH:N.NriC,5lI5 + C0rir>N2Cl - ri^T rn r/N:N-c«IT« i- - ^L5.co.c^N<N1LCyIr_ + Acetyl cliphenyl formnzyl. The third is capable of the utmost variety, since the sodium in the sodium compound may be removed by the action of : i. Iodine, which leads to the formation of acetosuccinic ester, CHo.CO.CHNa.COOCoII, " ' CH3.CO.CHNa.COOC.2irs CH,.CO.CII.COOCJIr L, = ' | ~ '+ 2NaI. " CH^.CQ.CII.COOCJL, Acetosuccinic ester. 2. Alkyl iodide, whereby two atoms of hydrogen may be successively replaced by the same or different radicals, CH.,.CO.CHNa.COOCoH, + CH,I = CH3.CO.CH(CIL)COOC,I I* '+ Nal. CHn.CO.CNa(CFI,}.COOCoII5+ CH3I =CH^CO.C(CIL,).,COOC>I U, ' + Nal. 3. Acid chloride, which is of similar character to the fore- going process, but gives rise in some cases to the simultaneous formation of two isomeric compounds, a fact which at one time threw considerable doubt on the ketonic character of acelo- acetic ester. Thus chloroformic ester and sodium acetoacetic ester produce the following two derivatives, of which the second predominates : CH3.CO.CH(C02C2H5)2. Acetylmalonic escer. CHS. C(OC02C2Hs) 'CH. COoC2I I5. jS-Carboxethylacetoacetic ester. The synthetic capabilities of this compound are not yet exhausted. Acetoacetic ester and its alkyl derivatives undergo decomposition in two ways, according to whether dilute alkalis and acids or, on the other hand, strong alkalis are employed.